Holly Madison Opens Up About Playboy Mansion Sex Life, Reveals Details of Hefner’s Will
Former Playboy model Holly Madison, now 45, has once again offered a glimpse into her life at the Playboy Mansion, this time focusing on her intimate relationship with Hugh Hefner and the complexities surrounding their dynamic. In a revealing interview on the podcast "In Your Dreams," Madison discussed her bedroom experiences with Hefner, contrasting private moments with the orchestrated group activities that she found deeply unsettling. She also touched upon her initial inclusion in Hefner’s will and the circumstances surrounding her departure from the mansion.
Madison’s time at the Playboy Mansion has been a frequent topic of conversation, often characterized by her candid descriptions of the environment and her personal experiences. This latest interview provides further insight into the nuanced and often contradictory aspects of her relationship with Hefner, who passed away in 2017 at the age of 91.
When questioned about Hefner’s performance in bed, Madison distinguished between their private encounters and the group sex sessions that were a hallmark of the Playboy lifestyle. "Well, it’s a very different story between when we were just, like, by ourselves than with everybody else in the room," she explained. Her disdain for the group activities was palpable. "Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it."
Madison’s strong aversion to these shared sexual experiences is not new. She has previously spoken about feeling pressured and uncomfortable in such situations, highlighting the power imbalance that existed within the Playboy Mansion. Her willingness to openly express her discomfort, even within that environment, speaks to her personal strength and her eventual decision to leave the lifestyle behind.
In stark contrast to the group settings, Madison described her private moments with Hefner as "a lot more normal than you would think." This admission, however, was met with skepticism by podcast host Owen Thiele, who responded, "I would not think it would be normal, to be honest." Madison countered, "Nobody does. I think everybody has this, like, real horror story of like, how gross an old man’s body must be."
Her defense of their private encounters, even while acknowledging the general perception of older men’s sexuality, reveals a complex understanding of her relationship with Hefner. It suggests that while she found the group dynamics repellent, she experienced a different kind of intimacy and connection with him when they were alone.
The conversation then shifted to the topic of Hefner’s will. Madison disclosed that she was initially included in the document, set to inherit a substantial sum of money. "I was put in the will at one point," she revealed. "And this is kind of sad. But when I broke up with him, I was packing my stuff. And then one day … there was a folder set out on my side of the bed because he knows I’m going to look at it. Like everybody knows I’m the biggest snoop in the house."
The details of Hefner’s attempt to retain her are particularly poignant. "So I look at it, and it’s his will all printed out, all the details. This is who’s getting what and … he was leaving me $3 million," Madison claimed. "But it was kind of sad though, because I’d already broken it off with him, and he was trying to get me to stay. So it was kind of like a low-key bribe but also sad because he can’t, like, sit me down and talk to me about it."
Hefner’s indirect approach, leaving the will out in the open for Madison to find, speaks volumes about his personality and his inability to directly confront his emotions. It also underscores the power dynamics at play, where financial incentives were often used to influence relationships within the Playboy Mansion.
Ultimately, Madison chose to leave the mansion and declined the inheritance. "The Girls Next Door" star went her separate way and said she later earned the $3 million left behind on her own. This decision highlights her independence and her desire to build a life on her own terms, free from the constraints of the Playboy lifestyle.
Madison moved into the Playboy Mansion at the age of 21 and departed at 29, following the conclusion of "The Girls Next Door," the reality TV series that offered a glimpse into the lives of Hefner’s girlfriends. In 2016, she published her memoir, "Down the Rabbit Hole," which detailed years of alleged verbal and emotional abuse.
Looking back on her experiences, Madison cautioned aspiring models against blindly pursuing opportunities in Hollywood. She emphasized the importance of researching the industry and understanding the potential pitfalls. "I remember being 18 and 19 and thinking I was such a badass and that I could just take on the world and that I could have sex like a man and have no emotional attachment," she reflected. "But it’s really not like that. Doing things like that carries a lot of emotional weight. I think looking into people’s stories who are honest about all the sides of the industry is a really good thing to do. And look at some of the cautionary tales before you just dive in."
Her advice stems from her own experiences, which exposed her to the darker aspects of fame and the potential for exploitation. She encourages young women to be informed and to prioritize their emotional well-being when navigating the entertainment industry.
In addition to her podcast appearance, Madison is also launching season 3 of Investigation Discovery’s true-crime series, "The Playboy Murders," which delves into the tragedies and crimes associated with the Playboy brand. This project further demonstrates her commitment to examining the complex legacy of Playboy and the impact it has had on the lives of those involved.
